Thermal cycloaddition reaction of symmetrical and unsymmetrical α-diazo-β-diketones with 4-aryl-2-methyl-2,3-dihydro-1,5-benzothia/diazepines

✍ Scribed by Jiaxi Xu; Sheng Jin

• Publisher: John Wiley and Sons
• Year: 1999
• Tongue: English
• Weight: 193 KB
• Volume: 10
• Category: Article
• ISSN: 1042-7163
• DOI: 10.1002/(sici)1098-1071(1999)10:1<35::aid-hc7>3.0.co;2-#

✦ Synopsis

Symmetrical and unsymmetrical ␣-diazo-b-diketones undergo thermal Wolff rearrangements to generate ␣-carbonylketenes to participate as dienes in Diels-Alder reactions with 4-aryl-2-methyl-2,3-dihydro-1,5-benzothia/diazepines to give, where applicable, regiospecific cycloadducts, 4a,5,6,12tetrahydro -1H/1H, 7H -1,3 -oxazino[3,2-d][1,5]benzothia/diazepin-1-ones. A mechanism of formation of the regiospecific cycloadducts is suggested. ᭧ 1999